BR112020015713A2 - Composto piridazinol, derivado do mesmo, método de preparação, composição herbicida e uso do mesmo - Google Patents
Composto piridazinol, derivado do mesmo, método de preparação, composição herbicida e uso do mesmo Download PDFInfo
- Publication number
- BR112020015713A2 BR112020015713A2 BR112020015713-9A BR112020015713A BR112020015713A2 BR 112020015713 A2 BR112020015713 A2 BR 112020015713A2 BR 112020015713 A BR112020015713 A BR 112020015713A BR 112020015713 A2 BR112020015713 A2 BR 112020015713A2
- Authority
- BR
- Brazil
- Prior art keywords
- alkyl
- heteroaryl
- mhz
- aryl
- cycloalkyl
- Prior art date
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- -1 PYRIDAZINOL COMPOUND Chemical class 0.000 title claims abstract description 256
- 239000000203 mixture Substances 0.000 title claims abstract description 49
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 30
- 239000004009 herbicide Substances 0.000 title claims description 26
- 238000002360 preparation method Methods 0.000 title abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 180
- 238000000034 method Methods 0.000 claims abstract description 26
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 476
- 125000001424 substituent group Chemical group 0.000 claims description 375
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 171
- 229910052736 halogen Inorganic materials 0.000 claims description 153
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 145
- 125000001072 heteroaryl group Chemical group 0.000 claims description 143
- 150000002367 halogens Chemical class 0.000 claims description 141
- 125000003118 aryl group Chemical group 0.000 claims description 139
- 125000003545 alkoxy group Chemical group 0.000 claims description 102
- 239000000460 chlorine Substances 0.000 claims description 100
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 92
- 238000006243 chemical reaction Methods 0.000 claims description 88
- 125000000217 alkyl group Chemical group 0.000 claims description 85
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 76
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 74
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 73
- 241000196324 Embryophyta Species 0.000 claims description 70
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 68
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 61
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 61
- 229910052794 bromium Inorganic materials 0.000 claims description 61
- 229910052801 chlorine Inorganic materials 0.000 claims description 61
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 60
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 60
- 229910052731 fluorine Inorganic materials 0.000 claims description 60
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 56
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 55
- 239000001257 hydrogen Substances 0.000 claims description 55
- 229910052739 hydrogen Inorganic materials 0.000 claims description 55
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 54
- 239000011737 fluorine Substances 0.000 claims description 54
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 53
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 52
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 52
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 51
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 51
- 125000005843 halogen group Chemical group 0.000 claims description 48
- 150000002431 hydrogen Chemical group 0.000 claims description 48
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 48
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 47
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 45
- 125000001153 fluoro group Chemical group F* 0.000 claims description 45
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 44
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 44
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 43
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 43
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 42
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 42
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 42
- 125000003342 alkenyl group Chemical group 0.000 claims description 41
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 40
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 40
- 125000003282 alkyl amino group Chemical group 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 39
- 125000004104 aryloxy group Chemical group 0.000 claims description 37
- 125000000623 heterocyclic group Chemical group 0.000 claims description 36
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 36
- 125000001931 aliphatic group Chemical group 0.000 claims description 35
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 35
- 229910052760 oxygen Inorganic materials 0.000 claims description 35
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 34
- 125000001246 bromo group Chemical group Br* 0.000 claims description 34
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 33
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 33
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 31
- 150000002148 esters Chemical class 0.000 claims description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 30
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 30
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 28
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 27
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 26
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 26
- 125000000304 alkynyl group Chemical group 0.000 claims description 25
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 24
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 21
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 21
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 21
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 claims description 20
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 20
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 18
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 17
- 238000009472 formulation Methods 0.000 claims description 17
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 16
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 16
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 15
- 125000004414 alkyl thio group Chemical group 0.000 claims description 15
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 15
- 150000002923 oximes Chemical class 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 14
- 239000003112 inhibitor Substances 0.000 claims description 13
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 13
- 235000011181 potassium carbonates Nutrition 0.000 claims description 13
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 13
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
- 244000062793 Sorghum vulgare Species 0.000 claims description 11
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
- 235000021307 Triticum Nutrition 0.000 claims description 10
- 240000007594 Oryza sativa Species 0.000 claims description 9
- 235000007164 Oryza sativa Nutrition 0.000 claims description 9
- 240000008042 Zea mays Species 0.000 claims description 9
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
- 235000009566 rice Nutrition 0.000 claims description 9
- 229920000742 Cotton Polymers 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 235000010469 Glycine max Nutrition 0.000 claims description 8
- 244000299507 Gossypium hirsutum Species 0.000 claims description 8
- SQVRNKJHWKZAKO-PFQGKNLYSA-N N-acetyl-beta-neuraminic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-PFQGKNLYSA-N 0.000 claims description 8
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- XJHCXCQVJFPJIK-UHFFFAOYSA-M cesium fluoride Substances [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 claims description 8
- 235000005822 corn Nutrition 0.000 claims description 8
- 150000002170 ethers Chemical class 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 7
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 7
- WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 claims description 7
- LLWADFLAOKUBDR-UHFFFAOYSA-N 2-methyl-4-chlorophenoxybutyric acid Chemical compound CC1=CC(Cl)=CC=C1OCCCC(O)=O LLWADFLAOKUBDR-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 7
- 125000004696 alkyl sulfanyl carbonyl group Chemical group 0.000 claims description 7
- 125000005146 naphthylsulfonyl group Chemical group C1(=CC=CC2=CC=CC=C12)S(=O)(=O)* 0.000 claims description 7
- 235000011118 potassium hydroxide Nutrition 0.000 claims description 7
- YIVXMZJTEQBPQO-UHFFFAOYSA-N 2,4-DB Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1Cl YIVXMZJTEQBPQO-UHFFFAOYSA-N 0.000 claims description 6
- 240000002791 Brassica napus Species 0.000 claims description 6
- 235000004977 Brassica sinapistrum Nutrition 0.000 claims description 6
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 239000005575 MCPB Substances 0.000 claims description 6
- 101150039283 MCPB gene Proteins 0.000 claims description 6
- 235000011684 Sorghum saccharatum Nutrition 0.000 claims description 6
- 125000005360 alkyl sulfoxide group Chemical group 0.000 claims description 6
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 6
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 6
- 125000002837 carbocyclic group Chemical group 0.000 claims description 6
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 claims description 6
- WYEHFWKAOXOVJD-UHFFFAOYSA-N diflufenican Chemical compound FC1=CC(F)=CC=C1NC(=O)C1=CC=CN=C1OC1=CC=CC(C(F)(F)F)=C1 WYEHFWKAOXOVJD-UHFFFAOYSA-N 0.000 claims description 6
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 6
- 235000019713 millet Nutrition 0.000 claims description 6
- NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 claims description 6
- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical group ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 claims description 6
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 6
- AIAYSXFWIUNXRC-PHIMTYICSA-N (1r,5s)-3-[hydroxy-[2-(2-methoxyethoxymethyl)-6-(trifluoromethyl)pyridin-3-yl]methylidene]bicyclo[3.2.1]octane-2,4-dione Chemical compound COCCOCC1=NC(C(F)(F)F)=CC=C1C(O)=C1C(=O)[C@@H](C2)CC[C@@H]2C1=O AIAYSXFWIUNXRC-PHIMTYICSA-N 0.000 claims description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 5
- 239000002794 2,4-DB Substances 0.000 claims description 5
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 claims description 5
- 239000005504 Dicamba Substances 0.000 claims description 5
- 239000005507 Diflufenican Substances 0.000 claims description 5
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical group F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 5
- 108010081348 HRT1 protein Hairy Chemical group 0.000 claims description 5
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 5
- 239000005595 Picloram Substances 0.000 claims description 5
- 239000005618 Sulcotrione Substances 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 5
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 5
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 150000002443 hydroxylamines Chemical class 0.000 claims description 5
- KPUREKXXPHOJQT-UHFFFAOYSA-N mesotrione Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O KPUREKXXPHOJQT-UHFFFAOYSA-N 0.000 claims description 5
- 230000037361 pathway Effects 0.000 claims description 5
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 5
- 235000015320 potassium carbonate Nutrition 0.000 claims description 5
- IUQAXCIUEPFPSF-UHFFFAOYSA-N tembotrione Chemical compound ClC1=C(COCC(F)(F)F)C(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O IUQAXCIUEPFPSF-UHFFFAOYSA-N 0.000 claims description 5
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 5
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 5
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 4
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 239000005578 Mesotrione Substances 0.000 claims description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
- 239000005620 Tembotrione Substances 0.000 claims description 4
- 240000005592 Veronica officinalis Species 0.000 claims description 4
- 101100339555 Zymoseptoria tritici HPPD gene Proteins 0.000 claims description 4
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 4
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- OQZCSNDVOWYALR-UHFFFAOYSA-N flurochloridone Chemical group FC(F)(F)C1=CC=CC(N2C(C(Cl)C(CCl)C2)=O)=C1 OQZCSNDVOWYALR-UHFFFAOYSA-N 0.000 claims description 4
- MEFQWPUMEMWTJP-UHFFFAOYSA-N fluroxypyr Chemical compound NC1=C(Cl)C(F)=NC(OCC(O)=O)=C1Cl MEFQWPUMEMWTJP-UHFFFAOYSA-N 0.000 claims description 4
- KDHKOPYYWOHESS-UHFFFAOYSA-N halauxifen-methyl Chemical group NC1=C(Cl)C(C(=O)OC)=NC(C=2C(=C(OC)C(Cl)=CC=2)F)=C1 KDHKOPYYWOHESS-UHFFFAOYSA-N 0.000 claims description 4
- 230000002140 halogenating effect Effects 0.000 claims description 4
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 claims description 4
- ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052705 radium Inorganic materials 0.000 claims description 4
- IYMLUHWAJFXAQP-UHFFFAOYSA-N topramezone Chemical compound CC1=C(C(=O)C2=C(N(C)N=C2)O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 IYMLUHWAJFXAQP-UHFFFAOYSA-N 0.000 claims description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 3
- 241000219144 Abutilon Species 0.000 claims description 3
- 239000005535 Flurochloridone Substances 0.000 claims description 3
- 239000005563 Halauxifen-methyl Substances 0.000 claims description 3
- 235000011999 Panicum crusgalli Nutrition 0.000 claims description 3
- 239000005608 Quinmerac Substances 0.000 claims description 3
- 238000006069 Suzuki reaction reaction Methods 0.000 claims description 3
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 3
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 3
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 3
- CWKFPEBMTGKLKX-UHFFFAOYSA-N picolinafen Chemical compound C1=CC(F)=CC=C1NC(=O)C1=CC=CC(OC=2C=C(C=CC=2)C(F)(F)F)=N1 CWKFPEBMTGKLKX-UHFFFAOYSA-N 0.000 claims description 3
- 235000011056 potassium acetate Nutrition 0.000 claims description 3
- VQRYVKJGEDNMNC-UHFFFAOYSA-N 2-[[2-chloro-3-[2-(1,3-dioxolan-2-yl)ethoxy]-4-methylsulfonylphenyl]-hydroxymethylidene]cyclohexane-1,3-dione Chemical compound ClC1=C(OCCC2OCCO2)C(S(=O)(=O)C)=CC=C1C(O)=C1C(=O)CCCC1=O VQRYVKJGEDNMNC-UHFFFAOYSA-N 0.000 claims description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 2
- 235000013479 Amaranthus retroflexus Nutrition 0.000 claims description 2
- 244000237956 Amaranthus retroflexus Species 0.000 claims description 2
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- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- A—HUMAN NECESSITIES
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds
- A01N57/32—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds containing heterocyclic radicals
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
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- A—HUMAN NECESSITIES
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/14—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
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CN201810104963 | 2018-02-02 | ||
CN201810104963.4 | 2018-02-02 | ||
CN201811035352.5 | 2018-09-06 | ||
CN201811035352.5A CN110128352A (zh) | 2018-02-02 | 2018-09-06 | 哒嗪醇类化合物及其衍生物、制备方法、除草组合物和应用 |
PCT/CN2019/074315 WO2019149260A1 (fr) | 2018-02-02 | 2019-02-01 | Composé de pyridazinol, dérivé de celui-ci, son procédé de préparation, composition herbicide et son utilisation |
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US (1) | US20220312770A1 (fr) |
EP (1) | EP3747870A4 (fr) |
CN (1) | CN110128352A (fr) |
AR (1) | AR117187A1 (fr) |
BR (1) | BR112020015713A2 (fr) |
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EP3647308B1 (fr) * | 2017-06-26 | 2023-05-31 | Nippon Soda Co., Ltd. | Composé hétéroarylpyrimidine, et agent de lutte contre les organismes nuisibles |
CN111820224B (zh) * | 2019-04-22 | 2022-04-05 | 江苏清原农冠杂草防治有限公司 | 包含三氟甲基哒嗪醇类化合物的除草组合物及其应用 |
CN113754633B (zh) * | 2021-09-26 | 2023-05-05 | 中国农业大学 | 1-(6-取代嘧啶-4-基)-1,2,3,4-四氢喹啉类化合物及其制备方法和应用 |
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AT334133B (de) * | 1974-12-17 | 1976-12-27 | Chemie Linz Ag | Herbizides mittel |
DE3218976A1 (de) * | 1982-05-19 | 1983-11-24 | Lentia GmbH Chem. u. pharm. Erzeugnisse - Industriebedarf, 8000 München | Verfahren zur herstellung von phenylpyridazinverbindungen |
US5623072A (en) * | 1994-10-11 | 1997-04-22 | Monsanto Company | 3-phenylpyridazines, herbicidal compositions and uses thereof |
EP1426365B9 (fr) * | 2001-08-17 | 2009-10-21 | Mitsui Chemicals Agro, Inc. | Derive de 3-phenoxy-4-pyridazinol et composition herbicide le contenant |
CN101648914A (zh) * | 2009-09-07 | 2010-02-17 | 南开大学 | 6-甲基-3-(3,4-二氯苯胺基)-4-(3-三氟甲基苯基)哒嗪的制备及其除草活性 |
CN106316962B (zh) * | 2015-07-01 | 2020-03-10 | 中国科学院上海有机化学研究所 | 3-芳基哒嗪酮类化合物、制备方法、农药组合物及用途 |
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RU2020128758A3 (fr) | 2022-03-02 |
US20220312770A1 (en) | 2022-10-06 |
RU2020128758A (ru) | 2022-03-02 |
EP3747870A1 (fr) | 2020-12-09 |
EP3747870A4 (fr) | 2021-11-03 |
CN110128352A (zh) | 2019-08-16 |
AR117187A1 (es) | 2021-07-21 |
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